[18F] I had sex with my best friends older brother last night whilst she was upstairs, and it was the best sex ever.
So obviously had to post this on a throwaway.
Me and my best friends brother  have always had a flirty relationship with each other. From when we first met (2 years ago) we’ve always flirted with each other and he’ll tease me or he’ll catch me staring or he’ll tell me I’m cute or if I look hot or whatever but it’s never gone beyond that.
Anyway last night I stayed over at my friends house and his room is downstairs and hers is upstairs. I went into the kitchen to get a drink in the middle of the night and he came out and started talking to me and there was just so much sexual tension he was just wearing shorts and I was just in my (too small lol) pj’s and next thing I know we where in his room and he was fucking me. It was the best sex ever!! It was pretty rushed and quick and we had to be quiet but in the moment just knowing that we could be caught at any moment made it so much hotter. He text me earlier telling me he loved it too and he wanted to do it again.
I feel like a terrible friend though. I feel like I should feel super guilty but all I can think about was how good it felt and I just get horny thinking about him. But definitely the thrill of having sex with someone you ‘shouldn’t’ was just amazing for me and I feel like I’m gonna go back for more but I feel like I’m torn because of my friend?
jillythatsme: The same thing happened to me (23F) when I was 18. I pretty much lived at my best friends house and I eventually ended up hooking up with her brother. She definitely wasn’t too impressed but she wasn’t livid either. Eventually she didn’t mind if I hooked up with him, she just didn’t want the details.
Mellrish221: Well… depends on the friend.
She could be super offended that you violated some unspoken trust, thought thats all you hung out with her for, or any slew of issues really.
Or she could be cool about it and probably doesn’t wanna hear about it after you tell her.
SHOULD have talked to her beforehand to gauge her reaction. But now its either you tell her, or she finds out eventually.
PM_me-ur-pootang: Is this a shitty thing to do?
Was it hot as fuck to read and would I do it if I had the chance?
Imnotmyself125: Had hot sex, she’ll get over it. I was the brother, 17, my older sister brought a friend home from college, 20. My sister went out with her BF, the friend said she had to stay to study. I could not believe it, as soon as parents went out to a movie she started flirting. I thought she was just teasing, until she joined me in the shower.
HanBan30: I do think there are a couple of things to keep in mind if this is going to continue:
1. Be open and honest with your best friend. Don’t use her to get closer to him / pretend that you want to see her when its really him.
2. Just because he is a family member of someone you know, that doesn’t make him not a “random” hook up so be sure to have the STI talk / see results / use condoms, etc.
VTL_89: Well this was hot as fuck…
throwaway032200: I’ve been in the same situation ish. 4 years ago when I was 17 I fucked my best friends older cousin. I only met him twice while I was over at her house but we were instantly attracted to each other and it was obvious. I had added him on fb after meeting the first time and he messaged me, basically saying he wanted to do stuff and asked when the next time I’d be sleeping over was. It sounds a little creepy now. I kind of wanted to, kind of was like eh is this a good idea.
But I went to sleepover a few days later, let him know, and sure enough he just happened to be having a sleepover that night too. All three of us were in my friends theater room watching a movie, friend went to bed. Couldn’t have been more perfect. We both told her we wanted to finish the movie and she didn’t think anything of it. We fucked right there and it was kind of hot knowing my friend or her brother could literally walk in any sec.
I made him swear not to tell and surprisingly he never did. I never did. She still has no idea and I don’t ever plan on telling her bc I know she’d be upset and grossed out lol. Felt like a bad friend and what not but it was a long time ago and I’m over it now.
NervousBoy0905: How does he usually flirt with you and intiate?
Just taking notes . . . .
FancifulFlipflop: You should watch The Edge of Seventeen
Jay_Cee313: Its better to tell her than to continue and have her find out another way. Super fucking hot though, I agree. Keep up the good work lol
gamer_zzzz: Is there a reason your friend wouldn’t approve?
Evstar: I have been in sort of a similar situation, I dated my best friends little sister. I asked his permission to kiss her for the first time because I was afraid of what would happen if I kept it a secret from him. In the end we had a huge falling out over me making it official with her without him being completely ok with it yet. I thought at the time he was overreacting, but in hindsight I’ve learnt that everyone’s feelings have to be 100% considered, and if not you’re just being super selfish. Sure, the sex is just between you and the bro, but it’s your best friends family. I fuckin urge you to talk to your friend. Honesty is always the best policy. She might not care at all. She might laugh and say she’s always known it was gonna happen. If you want to get with her bro again, talk to her about it. Most likely scenario is she’ll be pissed off but thankful that you’re telling her. I have lived this. Please take my advice 🙂 Or, not get with him again. That’s the 2 options.
_SCHULTZY_: Talk to your friend. Leave out the sex you already had. Tell her you want to ask her brother out because you find him attractive. But that you don’t want anything to jeopardize your friendship. Reassure your friend that you two will remain close no matter what.
Go from there. Focus on reassurance and the future.
jj_2002_14: > It was pretty rushed and quick
Did you use a condom? Did you have one with you? Did he offer to use one? Could there be any consequences from this if you did not use protection?
ashyy1997: I wish I had friends with hot brothers
Fluffstein: Would the friend disapprove
ClassicSchmosbyy: OP, you should really watch this movie called Edge of Seventeen.
oliverjohansson: Previous tension plus vibe of the moment this is what makes quickies that intense. The problem starts when one person pulls a conclusion that it’s a great start into relationship and another that to fwb…
Friscolopter: I would be ok with one of my best friends dating my sister. (I don’t have one) I just wouldn’t want to hear about them having sex.
mimithecoolcat: Ahhh this reminds me of a similar experience I had. It was sooo hot and so sneaky… my friend ended up finding out and being super angry and did not approve. If I were to go back in time, I would have been much more stealthy. Lol the first time I had sex with him at their house we all had to go to church together the next morning because their dad was the pastor. Best of luck!! Enjoy it 😉
BapZrannigan: I am happy for you.. too much drama, not enough good times.
Wrong2wrong2: Sharing is caring
PM_me_yo__BOOBIES: Honestly I don’t see the problem. You’re both obviously consenting.
Tell your friend so it isn’t behind her back. She probably will think it’s gross but that’s because she’s his brother and doesn’t want to think about him having sex, at all. You won’t be able to tell her details going forward, but that’s probably fine.
nocuddles4me: You experienced something that thousands of romance books are based on. I’m so glad you had a great time.
Try not to feel like a bad friend. What you do sexually is not her business.
FraterPoliphilo: You’re not a bad friend.
Sanoteesperfect: There’s nothing wrong about it. If anything it’s better because you know and can trust him. Is it more socially acceptable for you to meet some random guy on Tinder who could be anything, even dangerous?
siegekevin31: OMG how could you
Nyctophobia230: Yep, this was a shitty thing to do to your friend.
Cilvaa: Plot twist: she heard you and thought it was hot.
Bjarnithorbragason: What a shitty friend you are.
aurillia: you don’t need her approval, you are both consenting adults.
That said you could always bring up the subject by asking her if she be okay with you going out on a date with him. If she says she is okay with it then everything is good, if she doesn’t want you to date him, the fuck her, she is not a true friend.
poo_window: Can’t help but think the brother is a bit of an arsehole for sleeping with his little sisters friend.
A dude sleeping with his friends little sister doesn’t annoy me. I think thats hot.
But an older brother should look after their little sister and her friends. It crosses a line for me.
Twisterpa: My opinion? Not a shitty thing, you’re adults and the only reason she would feel upset is if she’s insecure and projecting that on you.
The sooner people understand that people do what they want, the easier it will be. If she’s upset at you I would delegitimize her argument by asking what the real reason she’s upset is for.